Lithium hydroxide, monohydrate → HCID 21075077, compound

HRID 1374267Notes

Reaction equation

HRID 1374267 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([C:15]2[N:16]=[N:17][N:18](CCC#N)[N:19]=2)[CH:14]=1)[C:8]([O:10]C)=[O:9])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>C1COCC1.O.Cl>[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([C:15]2[N:16]=[N:17][NH:18][N:19]=2)[CH:14]=1)[C:8]([OH:10])=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 21075154HCID 21075154, compound

Product 1

HCID 21075077HCID 21075077, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Preparation H6, Step 4: To a solution of methyl 3-tert-butyl-5-(2-(2-cyanoethyl)-2H-tetrazol-5-yl)benzoate (500 mg) in 20 mL of THF cooled to 0° C. was added dropwise a solution of lithium hydroxide monohydrate (76 mg) in 5.0 mL of water. The reaction mixture was stirred at RT for 16 h. THF was removed under reduced pressure to give a yellow oil which was diluted with 10 mL of 1 N HCl. The aqueous phase was extracted with EtOAc (2×25 mL), and the extracts were combined, dried over Na2SO4, and concentrated to afford 3-tert-butyl-5-(2H-tetrazol-5-yl)benzoic acid. MS found: (M+H)+=247.

Workup

  1. customPreparation H6, Step 4
  2. customTHF was removed under reduced pressure
  3. customto give a yellow oil which
  4. extractionThe aqueous phase was extracted with EtOAc (2×25 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b310e346b10c4f16a676dc5fae62183b
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

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